US4908372AExpiredUtility

Antihistaminic piperidinyl benzimidazoles

91
Assignee: MERRELL DOW PHARMAPriority: Oct 13, 1988Filed: Oct 13, 1988Granted: Mar 13, 1990
Est. expiryOct 13, 2008(expired)· nominal 20-yr term from priority
Inventors:Albert A. CarrHsien C. ChengJohn M. Kane
A61P 43/00A61P 37/08C07D 401/06
91
PatentIndex Score
61
Cited by
7
References
26
Claims

Abstract

The present invention is directed to a new class of piperidinyl benzimidazole antihistamines which can be described by the following formula: ##STR1## wherein Y is represented by CO or CHOH; m is an integer from 1 to 2; R is represented by C 1-4 alkyl, C 1-4 alkoxy, halogen, hydroxy and hydrogen, X is represented by hydrogen, COOR 2 in which R 2 is represented by a C 1-4 alkyl, or X is an alkylene phenyl radical of the formula: ##STR2## wherein T is represented by CHOH, CO, O, or a direct bond; R 1 is represented by C 1-4 alkyl, C 1-4 alkoxy, halogen, hydroxy, 2,2-dimethyl ethanoic acid and hydrogen; n is an integer from 1 to 5; or a pharmaceutically acceptable acid addition salt thereof.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of the formula: ##STR20## wherein Y is represented by CO or CHOH: m is an integer from 1 to 2; R is represented by C 1-4  alkyl, C 1-4  alkoxy, halogen, hydroxy and hydrogen, X is represented by hydrogen, COOR 2  in which R 2  is represented by a C 1-4  alkyl, Or X is an alkylene phenyl radical of the formula: ##STR21## wherein T is represented by CHOH, CO, O, or a direct bond; R 1  is represented by C 1-4  alkyl, C 1-4  alkoxy, halogen, hydroxy, 2,2-dimethyl ethanoic acid and hydrogen; n is an integer from 1 to 5; or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       2. A compound according to claim 1, wherein X is represented by an alkylene phenyl radical of the formula: ##STR22## wherein T is represented by CHOH, CO, O, or a direct bond; R 1  is represented by C 1-4  alkyl, C 1-4  alkoxy, halogen, hydroxy, 2,2-dimethyl ethanoic acid and hydrogen; n is an integer from 1 to 5. 
     
     
       3. A compound according to claim 2, wherein T is represented by CO. 
     
     
       4. A compound according to claim 3, wherein Y is represented by CO. 
     
     
       5. A compound according to claim 3, wherein Y is represented by CHOH. 
     
     
       6. A compound according o claim 2, wherein T is represented by CHOH. 
     
     
       7. A compound according to claim 6 wherein Y is represented by CO. 
     
     
       8. A compound according to claim 6, wherein Y is represented by CHOH. 
     
     
       9. A compound according to claim 1 wherein said compound is 1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone. 
     
     
       10. A compound according to claim 1 wherein said compound is 1-[(4-fluorophenyl)methyl]-α-[1-[2-(4-methoxyphenyl) ethyl]-4-piperidinyl]-1H-benzimidazole-2-methanol. 
     
     
       11. A compound according to claim 1 wherein said compound is α-[1-[4-(1,1-dimethylethyl)phenyl]-4-hydroxybutyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole-2-methanol. 
     
     
       12. A compound according to claim 1 wherein said compound is 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinyl]-1-butanone. 
     
     
       13. A compound according to claim 1 wherein said compound is [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone. 
     
     
       14. A compound of the formula: ##STR23## wherein Y is represented by CO or CHOH; m is n integer from 1 to 2; R is selected from the group consisting of C 1-4  alkyl, C 1-4  alkoxy, halogen, hydroxy and hydrogen, and Z is represented by an amino protecting group. 
     
     
       15. A pharmaceutical composition comprising a compound according to claim 1 present in an antihistaminic quantity in admixture with a pharmaceutically acceptable carrier. 
     
     
       16. A pharmaceutical composition according to claim 15 wherein said compound is 1-[(4-fluorophenyl(methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone. 
     
     
       17. A pharmaceutical composition according to claim 15 wherein said compound is 1[(4-fluorophenyl)methyl]-α-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-1H-benzimidazole-2-methanol. 
     
     
       18. A pharmaceutical composition according to claim 15 wherein said compound is α-[1-[4-[4-(1,1-dimethylethyl) phenyl]-4-hydroxybutyl]-4-piperidinyl]-1-[(4-fluorophenyl) methyl]-1H-benzimidazole-2-methanol. 
     
     
       19. A pharmaceutical Composition according to claim 15 wherein said compound is 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-[]1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinyl]-1-butanone. 
     
     
       20. A pharmaceutical composition according to claim 15 wherein said compound is [1-[(4-fluorophenyl(methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone. 
     
     
       21. A method for the treatment of allergic diseases comprising administering to a patient in need thereof, an antihistaminic amount of a compound according to claim 1. 
     
     
       22. A method according to claim 21 wherein said compound is 1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone. 
     
     
       23. A method according to claim 21 wherein said compound is 1-[(4-fluorophenyl)methyl]-α-[1-[2-(4-methoxyphenyl) ethyl]-4-piperidinyl]-1H-benzimidazole-2-methanol. 
     
     
       24. A method according to claim 21 wherein said compound is α-[1-[4-[4-(1,1-dimethylethyl)phenyl]-4-hydroxybutyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole-2-methanol. 
     
     
       25. A method according to claim 21 wherein said compound is 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinyl]-1-butanone. 
     
     
       26. A method according to claim 21 wherein said compound is [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone.

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